


Double Trouble

by Wayward_and_Worn



Category: Supernatural
Genre: F/M, Sex Toys, Voyeur Dean Winchester
Language: English
Status: Completed
Published: 2019-02-18
Updated: 2019-02-18
Packaged: 2019-10-30 16:47:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,605
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17832365
Author URL: https://archiveofourown.org/users/Wayward_and_Worn/pseuds/Wayward_and_Worn
Summary: Hunter and lover of Dean Winchester receives a gift for a job well done from a friend.  Unfortunately for Dean, he's not home when she first opens it.  But he need not worry, she'll show him.





	Double Trouble

**Author's Note:**

> This was the very first story I posted over on Tumblr in 2017 as part of a Toys challenge. And I can tell. But the idea and the story were fun.   
> Enjoy!

                As you pulled into the mostly empty parking lot of the famous Bunny Ranch in Nevada, you couldn’t help but playfully reach forward from the back to tug at Dean’s hair and whisper in his ear, “Need to clear out the pipes first dear?”

                He scoffed indignantly, “I’ll have you know that we are consummate professionals.  This is a job, Y/N, a very important job, and we are hunters.  No, I don’t need to “clean out the pipes” as you so crassly put it.”  He parked near the door and killed the engine.

                “You rubbed one out at the gas station in Carson City, didn’t you?” Sam replied with a smirk.

                “You bet your ass.  Let’s go.”  Practically leaping out of the driver’s side.  Exchanging a look and a roll of the eyes, you and Sam also exited. 

                “I guess I’m just not enough, huh?  How CAN I hope to compete with an entire establishment of women just ready and waiting to bounce up and down on your thick, hard…”

                “Enough!”  Sam cried, putting his hands over his ears.  “I swear if you two keep this shit up I’m going to either shoot you, or myself.”

                The three of you headed inside where Stacy, stage name “Glitter”, had clearly been pacing, and likely smoking cigarettes end to end.  She ran to you and threw her arms around your neck.  “Y/N!!  I knew you’d come!  I knew you’d believe me!”

                “Of course,” you replied, holding her at arm’s length as the boys approached.  “Stacy.  Also known as Glitter… this is Sam and Dean Winchester.  My partners.  Partners, this is Stacy, my college roommate.  A million years ago.”

                “Hey.” The Winchesters said in unison.  It was flat out creepy sometimes.  Stacy spent a moment looking both of them up and down.  Sam focused on his feet, while Dean studied her right back. 

                “So are you one of the… are you a…”  Dean faltered.

                “Hooker?”  Glitter replied with a laugh.  “Oh no, handsome, I’m THE hooker.  I’m the Madam.  Unlike your girl here, I actually use my degree.” 

                “Degree?”  Dean’s eyebrows were raised, as Sam’s head snapped up.  “They have degrees in-“

                “She was a business management major, dipshit.”  You replied quickly before Dean managed to offend one of the few people you had left on Earth.  Or simply got you all shot; there were some pretty dangerous characters that came through here. 

                “I love my job.  And I pitch in sometimes so I’m not working until later, handsome.”  You not-so-gently nudged her, “but you’re taken, aren’t you?”

                Dean smirked at you, “Completely.  Now Sammy here…”

                “So, who’s all been murdered around here?”  Sam blurted an octave too high. 

_A Few Days Later…_

                The three of you were headed out through the main parlor.  Of course the job wasn’t as easy as first thought.  A disgruntled pimp ghost with wicked hand-to-hand skills managed to drop you with a shot to the knee, causing Dean to lose his mind and empty EVERY iron round into the ghost while Sam completed the salt and burn.  Fortunately, said pimp was buried in the weeds out back.    

                You were trailing behind as your new limp slowed you considerably.  As you passed the bar, Stacy literally came out of nowhere and thrust a gift wrapped box into your hands.  Leaning in with a smile, she whispered, “You, and a man like that...” she gestured towards Dean, who was waiting for you. “You deserve stories that can’t even be told in the bar.” 

                “Honey,” you began, “You’ve seen what we do.  We can’t tell ANY stories in the bar.” 

                “Yeah, but you deserve stories that would make ME blush.  I know you know what I mean.”    With another glance back at Dean, she leaned in and kissed you full on the mouth.  “Thank you.  I love you.  Please stay alive.”  Raising her eyebrows at you once again, “Come back and play someday,” she smiled and turned away; disappearing into the complex. 

                You heard a strangled squeak come from the door where you could see Dean’s wide eyes, and very possibly, erection.  His mouth was hanging open just a bit.   As you limped towards him, he reached out and took your duffle you.  “That was so hot,” he gulped. 

                Tucking the gift under your arm, you brushed past him as you headed to the car.  Taking care to press against his groin.  Yup.  Erection.  “Hmmm, cherry chap stick.” You said, under your breath. 

                “You’re gonna pay for that.”  He growled.

                “I’m sure.”

_A Road Trip and A Few Hours Later…_

                “Honey, your knee is blown.  You’re better off staying here!”  Dean kissed your forehead softly, making you pout even more earnestly.  You’d just gotten back to the bunker when another hunter had called Sam for some Winchester style backup.  You HATED being away from him.  “It will only be a couple of days.”  He moved to the other end of the table and continued re-packing his bag.  You hobbled over to his side. 

                “It’s so empty in here when you’re gone.”  You said simply. 

                Looking up at you, and cocked his head, “You mean, in the bunker, right?”  He raised an eyebrow at you as his eyes began to sparkle.

                You blinked stupidly at him for a second and as you realized his joke, a shit-eating grin spread across his face.  You punched him in the gut and were rewarded with a “WHOOF” as the air rapidly left his lungs.  “Fine, go hunt your shapeshifter, I’ll just stay here and rot.  AND, for that I’m not opening the box from Stacy until you’re gone!”

                “Oh, my god, woman.”  Dean grabbed you by the waist and pulled you flush against him.  “I will miss the HELL out of you, Y/N” as he captured your lips for a kiss that made you absolutely believe he meant every word.  

_Later…_

                A few days turned into a week, a week turned into two, when they realized that it was a pair of shifters that just kept turning into each other.  “It’s like friggin’ Ghost and the Darkness out here,” Dean had growled into the phone. 

                “If you die on me…” you began.

                “I’m an incubus, and I’m yours.” He had answered.

                “I actually believe you.  It’s ok though, while you’ve been gone, I’ve been keeping busy with Big Blue here.”

                Silence.  You could hear his mental wheels spinning.  “Are you-?!” you heard the car door slam as Sam must have returned.  Hushed now, “Are you using the hooker toy?!  Big Blue?!  What is that?!”

                “Mmmm,” you replied in what you hoped was a sultry voice.  “It’s truly a gift.”

                “YOU OPENED THE BOX!!”  As much as Dean Winchester could whisper-shout, he did.  You tried your damndest not to laugh in his ear. “Y/N,” he breathed heavily, “I – we’re coming home tomorrow if I have to nuke the city.”

                Turns out Dean lied.  They were home that night.

                You were almost to the stairs when Dean hopped the railing halfway down and hit the ground running.  Ducking down as he approached you, he hit like a linebacker and threw you over his shoulder, and running down the hallway to your room. 

                “Welcome back Sammy!”  You hollered down the receding hallway. 

                “Hey Babe!” he called back, laughter coloring his voice, “Do we have any food?!”

                “YES!” you shouted as Dean crossed the threshold of your room and kicked the door closed.  Tossing you on the bed, he immediately blanketed your body with his, and smothering you with a kiss.  

                “I missed you.  I missed you so much.  How is your knee?  Are you ok?  Oh my god I hate being away from you.”  Without even giving you a chance to answer, he covered your lips with his again.  Tongue frantically dancing with yours as the temperature rose between you. 

                When he finally let you up for air, you dug your nails into his shoulders, then tugging at his flannel to remove it.  “My knee is better.  I’m so glad you’re home.  I missed you too.  So very much.”

                Shrugging out of the flannel and t-shirt, he leaned back and sat on his knees, between your legs.  Panting, he raised his hands in a “Well?” gesture, looking down at you.  “Where is it?”

                “Where is what?”  You braced yourself on your elbows to admire his chest.  An ugly bruise had formed on his shoulder.  Regardless, Dean Winchester was perfect.  And he was all yours. 

                Grabbing your hips and sliding you roughly up his lap so you could feel his bulge, already straining, “The blue thing.” he leaned back in for another kiss.

                “I don’t need it now.  I’ve got you.”  Grinding against him, getting the low groan you were looking for.  “Besides, it’s not like I keep it in my ass.  Where did you get that bruise?”

                Pausing only for a moment to trail his tongue across your jaw and down your neck.  “Ran into Sam.”  His head snapped back up, “You put it in your…” His pupils blew wider as he stared hungrily into your eyes.  You couldn’t hold in the laugh that escaped, the vibration coursing through you and to him where you were joined, he moaned softly, closed his eyes, and dropped his head to your shoulder.  “Missed this…” he whispered.

                Running your hands slowly up and down his back, “I missed you.” 

                “Please Y/N, show me.”  His voice was as close to begging as you’d ever heard him.  It was almost a whine. 

                Oh hell.  “You _really_ want to see?”  You whispered in his ear, suddenly deciding if he wants this, then dammit, he gets it and he’s going to be sorry.  “You want to watch me use the Double Trouble Dildo from Stacy?”  Rolling your hips up into him again, you felt his breath race over your neck. 

                “Yes.”  He gasped. 

                Running your hand across his shoulder and up into his hair, you grabbed a fistful, and gently pulled his head up to look directly at you.  “Then go sit in the chair.  No touching.  Only watching.”

                His growl turned into a reluctant groan as he kissed you once more.  After a moment, he heaved himself away from you, and walked, painfully, you noted, to sit in the desk chair.  As he dropped into the leather, he unbuttoned and reached into his jeans to adjust the erection that had NO chance of going away any time soon. 

                You stood, closed your eyes, and undressed slowly, pretending that you were alone in the room and that Dean was hundreds of miles away.  You thought about how much you missed his mouth on yours.  His hands on your skin.  How you loved the sounds of his breathing, grunts, and groans that escaped while you pleasured each other.  Keeping your eyes closed, you lay back on the bed.  You ignored the fact that you could feel Dean’s eyes burning hungrily into you. 

                You gently caressed your skin, starting at your throat, dragging your fingertips lightly down your body to you breasts.  Softly tweaking your nipples until they were hardened and aching.  You allowed your breathing to start coming heavier.  Imagining that they were his hands, you twisted your hips a little as you felt a slight rush of wetness.  Did you hear a gasp?  Was that you?  Or someone…no, of course not.  Dean was miles away. 

                Your right hand drifted lower, to your folds that were neglected for so long without him.  Imagining it was his fingers gently ghosting over the outer mound, pushing in slightly, testing the amount of desire, brushing past your clit that was already hardened and sensitive.  You had to bite your lip to not gasp his name as you tended to do.  You could swear you heard your name whispered.    

                You rolled over to your side, away from Dean, reaching into the drawer next to the bed, and pulled out what you had called “Big Blue.”  It was a bright blue, 17” double headed dildo.  Rolling onto your back, you heard a sharp intake of breath from your watcher.  Holding one end above your mouth, you stuck your tongue out, just touching the tip.  You then opened your mouth fully, taking in the cool head, sucking on it, imagining it to be Dean.  You pumped it in and out a few times for good measure.  Your watcher tried in vain to suppress the groan that escaped, causing you to smile around the toy as you slid it out of your mouth and licked along the side.     

                You were momentarily distracted by shuffling and the sound of a zipper off to the side, but you forced your eyes to stay shut.  It was no mystery what was going on.  All that mattered was that it was working.  You were driving him crazy.  You imagined him sitting in the chair, naked now, erect, eyes locked on your body.  Another surge of wetness between your thighs as this time you know you heard your name fall from his perfect lips.    

                Removing the dildo head from your mouth you dragged it down between your breasts, circling each nipple, then continuing between your legs.  You dropped one leg off the bed, placing your foot flat on the ground, also turning your hips a little towards the desk chair and its tortured occupant. 

                Using one hand, you parted your folds and with exaggerated slowness, and slid the dildo head in.  Using the natural curve of the toy, pushed until it brushed over your g-spot and a little bit past.  Your hips arched a little involuntarily, and your foot on the ground dug in a little.  Tightly grasping the other end, you twisted your wrist and the smooth toy moved in and out.  Using your leverage, you arched up to meet the thrusts as you pushed the dildo further into you.  You slowly fucked yourself until you were writhing, sweating, and your breath coming in gasps that you were quickly losing control of.  Finally, turning your head and opening your eyes, you see Dean’s emerald ones shining with desire.  He’s sweating too, his hand wrapped around his swollen member, stroking in time with you.

                That was your undoing, nothing on earth compared to the man watching you.  “Dean.”  You breathed. 

                He blinked, stood up, his hand not leaving his cock, and took a hesitant step towards you.  You could see the bead of precum on the tip.  “May I? “  He began.

                “Yes.”  You whispered and he closed the gap, gently resting the head against your lips where you pushed your tongue out, barely brushing, and tasting the salty drop as you whisked it away.  He placed the palm of his hand between your breasts, pushed down towards your stomach, and covered your hand that was controlling the dildo. 

                “Let me.”  His passion choked voice was more of a command than a question.  You let your hand fall to your side as he pushed the dildo in and out with a faster pace than you were using.  You moaned his name as you leaned towards his cock, taking as much into your mouth as you could.  “Y/N!  Fuck!!”  He cried in surprise, dropping the toy in the process.  “That’s enough.”  He muttered, grasping the end and gently easing Big Blue out and away from you.  Tossing it on the other end of the bed, he bent down to you, kissing you deeply, weeks of pent up passion translating through his frantic tongue.  Joining you on the bed and settling between your thighs, right where he belonged.

                “I’ve seen enough.  Please Y/N.  _Let_ me.”   Dean breathed.  


End file.
